Ethanol → HCID 18003572, compound

HRID 479148

Reaction equation

HRID 479148 reaction equation
[CH:1]([O:4][CH2:5][C:6]([O:8]CC)=[O:7])([CH3:3])[CH3:2].C(O[C@@H]([CH2:20][C:21]1[C:26]2[S:27][CH:28]=[CH:29][C:25]=2[C:24]([O:30][CH2:31][CH2:32][C:33]2[N:34]=[C:35]([C:39]3[CH:44]=[CH:43][C:42](C(C)C)=[CH:41][CH:40]=3)[O:36][C:37]=2[CH3:38])=[CH:23][CH:22]=1)C(O)=O)CC=C.[H-].[Na+].BrC[C:52]([OH:54])=O.C[CH2:56][OH:57]>CC(O)C>[CH3:56][O:57][C:41]1[CH:40]=[C:39]([C:35]2[O:36][C:37]([CH3:38])=[C:33]([CH2:32][CH2:31][O:30][C:24]3[C:25]4[CH:29]=[CH:28][S:27][C:26]=4[C:21]([CH2:20][CH:5]([O:4][CH:1]([CH3:2])[CH3:3])[C:6]([OH:8])=[O:7])=[CH:22][CH:23]=3)[N:34]=2)[CH:44]=[C:43]([O:54][CH3:52])[CH:42]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 537908Ethyl isopropoxyacetateHCID 69556375HCID 69556375, compound

Product 1

HCID 18003572HCID 18003572, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

was prepared in analogy to example 39, but using in the aldol-coupling step ethyl isopropoxy-acetate instead of butyl butoxy-acetate as white crystals of mp. 148-150°. The former reagent was synthesized as described above for but-3-enyloxy-acetic acid (see example 65) from iPrOH, NaH, and bromo-acetic acid, followed by acid catalyzed esterification with EtOH.

Workup

  1. customwas prepared in analogy to example 39
  2. customThe former reagent was synthesized

Sources & evidence

ORD record
ord-1d3e39c5ea0a4de897ae8f9539fa04a3
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Linked notes

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